On the crest of windsurfing stardom, Robby Naish finds the good life on Maui

Adjectives like cautious and conservative are not usually assigned to men who make a living streaking down the faces of 50-foot waves, but it is exactly how Robby Naish, 23-time world champion in windsurfing, describes his method.

“I have always been real conservative about my approach,” says Naish, who won his first world title at age 13. “I always handled myself like it could all end tomorrow, there wasn’t a path to follow, nothing was ever guaranteed.

“I wasn’t so much the pioneer that would go out there and try new stuff as the guy who would really put in the effort and try to perfect it. I was very focused on not getting hurt my whole career; I was focused on longevity. Until someone else did a trick, I usually waited until I knew it was possible, then I would go practice it like hell and try to master it.”

The ride to fame started at Kailua Beach where the young Naish would spend his days surfing or sailing little 12-foot Hobie cats. A chance encounter with a couple of windsurfers when he was 11 set him on his path to greatness. A short two years later he was winning his first world championship as an amateur, and five years after that he was graduating from high school at the same time windsurfing opened its first pro tour in 1981.

“So I deferred admissions to college for a year and said I’ll give this a try and I’m still giving it a try,” says Naish, who no longer competes but does surf competitions promotionally. “I have gone from being the youngest professional to the oldest professional.”

It is this mindset that led him to not just the top of the competitive world of windsurfing, but to the top of its business as well. Naish Sails is doing business in more than 60 countries now, and he has offices on both coasts and in Maui offering all things ocean-related from stand up paddle boards to kite surfing equipment.

Despite his success, you still won’t find him in an office — because frankly, he doesn’t have one.

“If you go to our headquarters, I don’t have a desk, I’ve got no phone extension, I’m fairly elusive,” says Naish. “I am very involved in all the divisions, but not to the point where you can walk in and find me sitting behind a desk. My priority is still to be out on the water and be the face of the company. Even for the good of the brand my value is best served juggling all those responsibilities rather than answering emails all day.”

When he is not in the water, you can find him at his new palatial estate in Haiku, Maui. Built just over two years ago, the 7,200 sq ft home is situated on its own peninsula overlooking the Pacific Ocean. The home is at the top of the 73-acre property, so that when one looks out the backdoor to the rolling fields and the Pacific Ocean beyond, it seems to stretch on forever.

Two hundred-foot sea cliffs line the property with pathways down either side to access the fertile fishing grounds. Between the cliffs and his home is the grazing land for his cattle, which number between 20 to 50 head depending on the time of year, and he has crisscrossed the pasture with ATV tracks for visiting kids.

“I wanted to get a piece of Hawaii before it was all gone,” says Naish, “and I am glad I did it because eventually it will be one of the few preserved big pieces of land; we have no intentions of cutting it up.”

The home itself has a timeless design to it, taking elements from the Moana Hotel for its entryway, pillars from a 19th Century design on Oahu and tons of lava rock filling the walls and pool area. They spent two years building it, with Naish’s wife Katie in on each step.

“Katie designed every inch,” says Naish of his wife of 17 years. “She can literally tell you to an inch the dimension of every wall in the house, which is a trip. That’s how involved she got in micromanaging it, but it really came out great as a result.”

While Katie may have the house, Naish has got his barn. One wall is lined with nothing but boards and booms in every imaginable size, while a good part of the floor is taken up by his other passion: cars.

First is his ’63 Cadillac Hearst, with blowers sneaking out from underneath. Naish loves it because it is the one car that can fit all his gear in it. Next you will find his Porsche and his crown jewel, a 1991 canary yellow Evans Series 1 street legal racecar.

“I love my cars, but I just don’t have the time for them,” says Naish, who also owns “the biggest truck on Maui” with his lifted Ford F-250. “What I need to find is a friend who is a mechanic who will come over and drink beers and work on the cars at night, but I haven’t found him yet.”

Behind the barn, however, may be the most important equipment on the property. There, his former kite designer, Tom Montague, is using what was to be a field for crops to work on an alternative energy source using kites. The theory is to use high power traction kites at high altitudes, tacking them back and forth causing them to generate an enormous amount of power.

The company is named Makani Power and has a financial backing of $25 million from Google founders Larry Page and Sergey Brin. So instead of corn, Naish has weather towers and wind gauges sprouting from the ground in his field.

“I would really love to get this place off the grid,” says Naish. “If the kites don’t work, we’ll put in windmills.”

Beyond helping the environment, Naish looks to better the world by being a member of the Laureus World Sports Academy. This is an organization that looks to help the youth of the world through sports and has such luminaries as Jack Nicklaus, Dan Marino and John McEnroe as members.

“We provide both money and awareness to existing programs around the world that are youth sport-related programs,” says Naish, of the London-based organization. “Rather then us going out and creating projects in countries, we find projects, like in Brazil with gang-related youth or the midnight basketball league in Virginia. We are using the power of sport to promote social change in the world for young people with various political, social and economic problems.”

At home he has a new youth project all his own with the arrival of his daughter Christina a little over a year ago. Being a dad may not have slowed down his charging spirit, but it does give him pause when he is looking at surfing big waves.

“It’s a calculated approach, I’ve gone down at Jaws as hard as anybody,” says Naish, whose home is about a mile from this notoriously big surf break.

“You push the limits enough so that you know what’s going on, then you step back a little bit. But now with Christina I am even more cautious than I was before. People would look at me and think I was crazy, but you just raise your level of awareness, perception and ability to the point where you may look absolutely insane, but you’ve got all the variables pretty much down to the point that the risk is calculated so much that its pretty easy. But with her now, I am really not wanting to step over that line.”